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16.16.5.5.1 Phenazines by Ring Contraction of 10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepines

DOI: 10.1055/sos-SD-116-01265

Ambhaikar, N. B.Science of Synthesis Knowledge Updates, (20202214.

Chemoselective cleavage of CC and CN bonds is typically a challenging objective, where traditional methods involve harsh conditions and expensive or toxic metals in combination with oxidants. In principle, these methods can bring about cleavage of CC and CN bonds in 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines, followed by the formation of a new CN bond, leading to the corresponding phenazines. Scheme 22 shows the concept behind a possible transition-metal-free tandem oxidative removal of a benzylic methylene group by CC and CN bond cleavage, followed by intramolecular formation of a new CarylN bond under radical conditions.

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